共 59 条
Asymmetric synthesis of pyrrolo[1,2-a]indoles via organocatalytic [3+2] annulation of substituted 2-vinylindoles with azlactones
被引:15
作者:

Yang, Wulin
论文数: 0 引用数: 0
h-index: 0
机构:
East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Sch Pharm, Shanghai 200237, Peoples R China East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Sch Pharm, Shanghai 200237, Peoples R China

Wang, Hao
论文数: 0 引用数: 0
h-index: 0
机构:
East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Sch Pharm, Shanghai 200237, Peoples R China

Pan, Zirong
论文数: 0 引用数: 0
h-index: 0
机构:
East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Sch Pharm, Shanghai 200237, Peoples R China

Li, Zhong
论文数: 0 引用数: 0
h-index: 0
机构:
East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Sch Pharm, Shanghai 200237, Peoples R China
Shanghai Collaborat Innovat Ctr Biomfg Technol, Shanghai 200237, Peoples R China East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Sch Pharm, Shanghai 200237, Peoples R China

Deng, Weiping
论文数: 0 引用数: 0
h-index: 0
机构:
East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Sch Pharm, Shanghai 200237, Peoples R China
机构:
[1] East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Sch Pharm, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China
[3] Shanghai Collaborat Innovat Ctr Biomfg Technol, Shanghai 200237, Peoples R China
基金:
中国博士后科学基金;
关键词:
3+2] Annulation;
Azlactones;
2-Vinylindoles;
Asymmetric organocatalysis;
Pyrrolo[1,2-a]indoles;
Chiral phosphoric acid;
ENANTIOSELECTIVE SYNTHESIS;
AZOMETHINE YLIDES;
BRONSTED ACID;
CASCADE REACTION;
ACCESS;
CYCLOADDITION;
DIHYDROCOUMARINS;
CONSTRUCTION;
DERIVATIVES;
ALKYLATION;
D O I:
10.1016/j.cclet.2019.09.008
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
The chiral phosphoric acid catalyzed asymmetric [3 + 2] annulation of substituted 2-vinylindoles with azlactones has been established. This reaction represented a practical approach for the synthesis of structurally diverse pyrrolo[1,2-a]indoles with two vicinal stereocenters including one tetrasubstituted stereocenter in good yields and good stereoselectivities under mild conditions. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:721 / 724
页数:4
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共 59 条
- [1] Stronger bronsted acids[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758Akiyama, Takahiko论文数: 0 引用数: 0 h-index: 0机构: Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
- [2] Bronsted Acid Catalyzed [3+2]-Cycloaddition of Cyclic Enamides with in Situ Generated 2-Methide-2H-indoles: Enantioselective Synthesis of Indolo[1,2-a]indoles[J]. ORGANIC LETTERS, 2016, 18 (21) : 5660 - 5663Bera, Kalisankar论文数: 0 引用数: 0 h-index: 0机构: Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, Germany Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, GermanySchneider, Christoph论文数: 0 引用数: 0 h-index: 0机构: Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, Germany Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, Germany
- [3] Bronsted Acid Catalyzed [3+2]-Cycloaddition of 2-Vinylindoles with In Situ Generated 2-Methide-2H-indoles: Highly Enantioselective Synthesis of Pyrrolo[1,2-a]indoles[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (21) : 7074 - 7078Bera, Kalisankar论文数: 0 引用数: 0 h-index: 0机构: Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, Germany Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, GermanySchneider, Christoph论文数: 0 引用数: 0 h-index: 0机构: Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, Germany Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, Germany
- [4] Enantioselective Intramolecular Aza-Michael Additions of Indoles Catalyzed by Chiral Phosphoric Acids[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) : 8666 - 8669Cai, Quan论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R ChinaZheng, Chao论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R ChinaYou, Shu-Li论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
- [5] Highly Enantioselective Friedel-Crafts Alkylation/N-Hemiacetalization Cascade Reaction with Indoles[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3250 - 3254Cheng, Hong-Gang论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R ChinaLu, Liang-Qiu论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R ChinaWang, Tao论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R ChinaYang, Qing-Qing论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R ChinaLiu, Xiao-Peng论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R ChinaLi, Yang论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R ChinaDeng, Qiao-Hui论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R ChinaChen, Jia-Rong论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R ChinaXiao, Wen-Jing论文数: 0 引用数: 0 h-index: 0机构: Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
- [6] Strategies for the asymmetric functionalization of indoles: an update[J]. CHEMICAL SOCIETY REVIEWS, 2015, 44 (03) : 742 - 778Dalpozzo, Renato论文数: 0 引用数: 0 h-index: 0机构: Univ Calabria, Dipartimento Chim & Tecnol Chim, Cubo 12-C, I-87036 Arcavacata Di Rende, Cs, Italy Univ Calabria, Dipartimento Chim & Tecnol Chim, Cubo 12-C, I-87036 Arcavacata Di Rende, Cs, Italy
- [7] Organocatalytic Oxyamination of Azlactones: Kinetic Resolution of Oxaziridines and Asymmetric Synthesis of Oxazolin-4-ones[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (27) : 10026 - 10029Dong, Shunxi论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R ChinaLiu, Xiaohua论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R ChinaZhu, Yin论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R ChinaHe, Peng论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R ChinaLin, Lili论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R ChinaFeng, Xiaoming论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
- [8] Asymmetric Synthesis of 3, 4-Diaminochroman-2-ones Promoted by Guanidine and Bisguanidium Salt[J]. ORGANIC LETTERS, 2011, 13 (19) : 5060 - 5063Dong, Shunxi论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaLiu, Xiaohua论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaZhang, Yulong论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaLin, Lili论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaFeng, Xiaoming论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China
- [9] Chiral Bisguanidine-Catalyzed Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Chalcones with Azlactones[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) : 10650 - 10651Dong, Shunxi论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaLiu, Xiaohua论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaChen, Xiaohong论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaMei, Fang论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaZhang, Yulong论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaGao, Bo论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaLin, Lili论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R ChinaFeng, Xiaoming论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China
- [10] Flinderoles A-C: Antimalarial Bis-indole Alkaloids from Flindersia Species[J]. ORGANIC LETTERS, 2009, 11 (02) : 329 - 332Fernandez, Liza S.论文数: 0 引用数: 0 h-index: 0机构: Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia Griffith Med Res Coll, Herston, Qld 4006, Australia Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, AustraliaBuchanan, Malcolm S.论文数: 0 引用数: 0 h-index: 0机构: Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, AustraliaCarroll, Anthony R.论文数: 0 引用数: 0 h-index: 0机构: Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, AustraliaFeng, Yun Jiang论文数: 0 引用数: 0 h-index: 0机构: Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, AustraliaQuinn, Ronald J.论文数: 0 引用数: 0 h-index: 0机构: Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, AustraliaAvery, Vicky M.论文数: 0 引用数: 0 h-index: 0机构: Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia Griffith Med Res Coll, Herston, Qld 4006, Australia Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia